


Fortune's Favor

by Lewdsmokesoldier



Category: League of Legends
Genre: Crossdressing, F/M, Feminization, Futanari, Mildly Dubious Consent, Other, could be interpreted as trans
Language: English
Status: Completed
Published: 2020-01-22
Updated: 2020-01-22
Packaged: 2021-02-27 08:07:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,184
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22363858
Author URL: https://archiveofourown.org/users/Lewdsmokesoldier/pseuds/Lewdsmokesoldier
Summary: It gets lonely out there on the high seas, and Sarah Fortune isn’t stupid enough to risk her crew’s disrespect by sleeping with any of them. Luckily, she’s brought on a gorgeous young man who’ll fit the role perfectly. Assuming he can handle what she has to offer.
Relationships: Miss Sarah Fortune/Original Character(s)
Kudos: 15





	Fortune's Favor

He always made sure to be pretty for his Captain.

The routine was comfortingly familiar by now. Washing, then a thick application of ruby lipstick, a dusting of powder, some curling of his eyelashes, a bit of mascara and eyeliner, some fluffing of his scarlet hair to get it nice and bouncy, and, of course, the appropriate clothes. He only really had one look he needed to capture, but when he did it properly, he could look at himself in the mirror and understand how he’d captured Sarah Fortune’s affections.

Tight brown-leather pants with splits along his svelte thighs. A tube top with bright lace on the upper half and frilly white gloves secured below his elbows with a maroon band. And topped with a gold-embroided captain’s hat. 

His smooth stomach and the entirety of his shoulders and upper arms were exposed, and the tube top was only held in place with a buckle around the back and some ribbons that hooked near where his biceps met his shoulders. What he wore did little to cover him, anyway. His pants were so tight that the outline of his mouthwateringly enticing rear was plainly visible from the back, pulled so low that the top of his pubic hair was visible from the front, and the top of his asscheeks from behind. The lack of stretching on his tube top and the absence of any indication of covered breasts were hints to the nuances of his identity, but when he got excited, the little bulge that sprouted from the front of his pants told the rest of the story.

His captain wanted him pretty, and therefore pretty he would be. He’d be the most heart-achingly beautiful woman on the high seas if it meant making her happy. Or he’d be the sluttiest, most wanton whore if that was what she wanted. She hadn’t asked that of him yet, but he would be ready when she did: he knew how the rest of the crew looked at him. Sarah Fortune guarded him jealously, but someday, maybe, she’d let the rest of her ship have their way with him.

Would they fall on him at once, or take turns? Would she leave him to them alone, or supervise, or participate herself? He didn’t know, but he didn’t really care, either, so long as it was what she wanted. Besides, being the ship’s slut, as well as the most gorgeous woman aboard, wasn’t mutually exclusive. He could quite easily be both, given that he was already Miss Fortune’s personal cock-socket while still maintaining a veneer of grace around the rest of her followers.

He was getting ahead of himself, anyway. Maybe they wanted him, but until his captain and Mistress gave him the order, he’d stay loyally hers and hers alone. But he wouldn’t deny how enticing it was to be so openly desired by everyone around him. Here, he could be what he’d really always wanted, even if he’d never known it. Here, he could be a woman, and here he could be happy. 

* * *

_It had started with a familiar story. A brash young man in Bilgewater like so many others, looking to sign on to a ship to find freedom outside of the Slaughter Docks._

_His efforts had been frustrated many, many times. The arguments were usually the same._

_“Too scrawny.”_

_“Too soft.”_

_“Too fragile.”_

_“Too sensitive.”_

_And that was if they even gave him the time of day._

_Finally, in despair, he had turned to the bold, fearless young woman who had captured so many hearts and minds in Bilgewater. He had kept his composure even as he made his case, and argued well for his place on her crew. Sure, he wasn’t the strongest or most experienced, but he had youth and he had energy, and those had to count for something, dammit._

_Captain Sarah Fortune, wavy hair hanging over eye, had looked him up and down. After a long, uncomfortable silence, she had grinned and extended a hand._

_“You’ve got a place on my crew. But it might not be the role you expect…”_

* * *

_The first hint he had gotten was when she had called him into her cabin on the first night of his service, while they were still in port._

_“I’m bringing you on to serve as a cabin boy, of sorts. You’ll help out the rest, but you’re mostly going to be working with me in here on personal matters.”_

_“Thank you, Captain.” His voice was high, soft, and sweet in its mellifluousness._

_“You’re already a redhead. That makes this easier. Hm...got turned away from the rest because you’re real slim, eh?”_

_“I…”_

_“It’s okay, I understand. Don’t worry about it, that won’t be a problem here. In fact,” Her stormy-gray eyes flashed with mirth, and she chuckled, “That’s pretty much the only reason I hired you.”_

_“I...I don’t understand, Captain.”_

_“You will.” She reached a hand out and stroked his cheek, brushing his hair behind his ear and tickling his chin. His face was completely smooth: he’d never been able to grow stubble, much less a beard, and she seemed pleased with the softness beneath her fingers. “Eventually. Now, my first order for you is to pretty yourself up a bit. If you’re going to be taking care of me in my cabin, I’m going to want you to be a step above the rest of the crew in the looks department. Well, more than you already are.”_

_He gulped, his throat bobbing beneath her fingers._

_“Aw, don’t fret, dear. What you need is in the box in the corner: I expect you to have applied it by the time I get back from roll-call.”_

_“Of course, Captain.”_

_After she left, he followed her direction, and wound up confused when he opened the box she’d pointed to and found it full of cosmetics. Had she misdirected him? But she had been very specific...and he didn’t want to upset her._

_So he went ahead and did his best. He smudged the lipstick a bit, and the mascara had gone past the corners of his eyes, and he’d gotten some powder stuck on his nose, but by the time he was done, he was marginally more tarted up than he had been before._

_Sarah Fortune had walked back in, took one look at his messily applied makeup, and nodded approvingly._

_“Good boy.”_

* * *

The soft _click-clack_ of her boots on the deck let him know that she was coming. He didn’t need to move: she preferred to see him at ease, rather than watch him rush to a position he thought she’d like. If his instincts were right, she’d want his mouth first, before anything else.

He puckered his lips, drew his tongue along his teeth, and batted his eyelashes as the door creaked open.

* * *

_Things had moved quickly from that point onward._

_Miss Fortune had him apply makeup regularly until he got used to using it well, and he was too worried about being left in the lurch to question her. Truthfully, he enjoyed it: it was liberating to be able to try things out in an environment where he wouldn’t be questioned, even if he’d never been drawn to do it before._

_It also meant that he didn’t have to participate in the same work that the rest of the crew did, but none of them dared talk down to him even when he awkwardly moved among them during meal times. He still didn’t know why, and it wasn’t until the first night after they set sail that he’d finally figured it out._

_He was sitting in front of her mirror, getting ready to check how he’d done with his daily application, when Sarah Fortune had turned from her desk, stood, and walked towards the door._

_“All right, I suppose it’s time to get down to business.” She said as she locked the deadbolt and turned back to him. On deck and in public, she cut an authoritative, imposing figure with her coat of blue and silver, a high-popped collar, a wide belt holding up her vertically-striped pantaloons, high-heeled boots, a white-trimmed corset and, of course, her magnificently proportioned hat._

_In her cabin, though, she’d shed most of the ostentation for a simple gray-tan long-sleeved shirt and leather pants secured with a smaller buckle. She still had those massive, knee-length, high-heeled boots, though._

_“I brought you on to help around the cabin and with the business and personal end of things, yeah. But the…’personal’ elements are a bit special. Do you follow me?”_

_“No, Captain.”_

_Miss Fortune sighed. “I suppose there’s nothing to it, then.” With a huff, she undid the belt buckle holding up her pants and pulled them down to the top of her boots, revealing what lay beneath._

_Not only was she not wearing any undergarments, but in the place of a pussy, a long, thick dick sprouted from her crotch with two fat balls hanging beneath, crowned with a tuft of pubic hair that matched the color of the locks on her head. It swung gently, half-erect and stiffening before his very eyes._

_The fact that she was in possession of such equipment was unexpected, to be true, but it wouldn’t have been the first time that he’d heard of such phenomena. Runeterra had a fairly large population of such women, to say nothing of those that acted independently outside of stratified boundaries of gender and sex, or those who counted themselves as members of cultures that didn’t adhere to binaries. He had never seen a dick and a pair of balls replace a pussy on a woman before, but he was well aware that it existed._

_No, what surprised him was that she was going ahead and exposing it to him right then and there. He blinked, gaped, and sputtered, trying and failing to form words in his confusion. She, meanwhile, just smiled and pulled off her top, her nipples catching on the fabric before they popped free with a hefty bounce. She tossed her shirt to the side, interlocking her arms and stretching backwards, sticking out her plump, weighty breasts and leaving her dick wobbling._

_“_ Ahhhh _, that’s the stuff. Been a while since I’ve let everything all out. What do you think?”_

_“I…”_

_“I asked you a question, honey.”_

_“I...um.” He knew what he_ wanted _to say, but did he have the courage to say it? Did he have the spine to actually give voice to his thoughts? His track record didn’t bode well on that front._

 _“You can’t keep your eyes off them, can you? I know you like ‘em, but I don’t just mean my tits. I mean my cock, sweetie, and the balls that are just_ churning _to let loose...I’m just surprised you didn’t figure it out before now.”_

_“Figure what out?”_

_“That I brought you on board to wrap around my cock and empty my nuts into, dear.” Sarah Fortune chuckled. “Surely you must have suspected, what with all my comments, and the makeup…”_

_He’d had some questions about why she was giving him such a specific command as ‘use my makeup on yourself’, but now the pieces fell into place. His softness and slimness and effeminacy, and her little remarks, and the prettying up…_

_“Now, be a good boy and suck my cock.” The freckles on her cheeks shifted with her wide, satisfied grin._

_“And if I say no?”_

_“I’m your captain, and that means you’re going to do as I say. I’m not going to throw you overboard, but I_ will _point out that we just left port, so...it’s going to be a long time before you’ll get the chance to get away from me. I’m also going to keep asking you until you say yes, so why not just get to the real reason I even brought you aboard? I promise it’ll be fun…”_

_In hindsight, he wanted to be able to tell himself that he had thought about it for a while, and that he had weighed both options and made a calculated decision based on a variety of factors. That he had struggled with the idea of giving in and giving up, if only for a moment, to quench the interest building up within him. That would have spared his dignity, and his conscience. But it wouldn’t have been true._

_When he knelt and leaned towards her dick, eyes fixed on that hypnotically twitching length and the fat nutsack that accompanied it, he was well aware that the answer was much simpler. He just wanted to have a taste. Just a little, to tide over his curiosity and get her off his back. He’d never done this before, and this wasn’t the worst environment it could happen in…and once it happened, he wouldn’t have to do it again, right? What could go wrong?_

_“Good boy.” Miss Fortune murmured as he extended his tongue to lap at the head of her cock. It was fatter than the rest of her dick, thicker and weightier. It certainly smelled nice, some sort of cocktail of sweat and salt air that left him feeling woozy in the best possible way. Rather than keep working her with his tongue, he instead dove for the spot where the scent was the strongest, burying length his nose in the folds of her scrotum, digging into her nutsack and breathing heavily to take it all in. His eyesight was blocked by a combination of her balls, her dick, and her pelvis, and he didn’t really care. Just so long as he got the chance to partake more of her…_

_He sniffed and licked and suckled on her fat, heavy nuts, and she sighed and crooned all the while. “Mmm. Enthralling, isn’t it? And that’s just the start, my dear. Why don’t you get back to work up top?”_

_Her fingers dug into his hair and she gently guided him up, back towards her cockhead. Two fingers pinched his nose, but his mouth was already open and ready, tongue extended to serve as a pillow while her shaft slipped between his lips, pushing down on the muscle while she leaned back and hummed in delight._

_“Ooh~” She panted, biting her lip. “Perfect, honey. Isn’t that much better?”_

_He couldn’t respond, but if his mouth was free, he might have said something to the affirmative, albeit not wholeheartedly. He was having a good time...but at the back of his mind, he needed to remember that this was a one-time thing, meant to tide her over so she wouldn’t go for this again._

_It never occurred to him that acquiescing so quickly would have the exact opposite effect._

_Miss Fortune fed him her cock, gently pumping her hips forward and back, her fingers tangled in his hair and stroking his cheek and blocking the air from his nostrils. He did his best to move with her, gulping and swallowing on her length while the warmth and wetness of his mouth did the rest._

_“Mmmf, grab my balls, sweetie.” She ordered, giving him a long, hard jerk of her waist forward, shoving her dick into the back of his throat so quickly that he gagged. “Rub the nuts that are gonna blast your throat.”_

_He did as she ordered, one hand on the base of her dick and the other cupping, squeezing, and stroking the nutsack he had so recently found himself under the influence of. He groped and prodded, and, sure enough, couldn't find a pussy behind those balls while she let him work. She still wasn’t going rough, but he could feel the strain on his jaw and tongue: he wasn’t used to this, not in the slightest._

_“Here it comes!” Miss Fortune crooned, giving him one more long, slow pump of her cock, deep enough for the head to tap the back of his throat and for his nose to push against her pelvis. “Hold still, and this’ll be nice and easy~.”_

_Just as promised, there was a rush of thick, wet heat as her balls tensed and tightened in his grip, her dick twitching in his mouth while she fired off her load. It shot out of her and splattered his tongue, firing further to ooze down his throat in a great, heavy flow of cum. He moaned around her intruding dick and tried to withdraw, but she held him fast, his nose buried in her frizzy pubic hair as he released her nuts from his hand to put his fingers on her thigh._

_“Nuh-uh.” Captain Fortune chastised, tut-tutting and tapping his forehead reproachfully while her nuts rested on his chin. “I’m not letting you ruin this. If you want to be good, you have to swallow it all. Every drop, dear. Just think of it as a sweet, warm, creamy treat~.”_

_He tried, and even though it wasn’t sweet, there was a pleasant saltiness to her load that urged him to bob his throat and suck it down, lips quivering on her shaft until she slid backwards and withdrew, a line of spunk connecting the head of her softening dick with his lips while he hacked and coughed, even though no spunk came out. Tears had welled up in his cheeks, forcing the mascara and eye makeup he’d so meticulously applied to run down his face in long lines of fluid that washed away the powder he’d used. Rings of red streaked across her cock from where his lips had pressed onto her skin a little too tightly. He had to look like a mess._

_“Well done.” She rubbed his hair demeaningly, swinging her dick to tap his nose. “A good first go. But don’t worry. You’ll get plenty of chances to practice. And plenty more helpings of my delicious cum!”_

_He gulped as she wiped her cock on his cheek and slapped him back and forth across the face with her softening cock, scattering drool and sweat everywhere, and he looked up between her heaving tits to glance at her beaming, freckled face. This was going to be a long trip…_

* * *

_Like before, he’d fallen into a routine._

_Every day, his captain, Sarah Fortune, had him please her with his mouth. More than once a day, usually, and twice in a row or more when she got excited._

_It had started off with sessions like the first, with him gingerly and tenderly exploring her cock and balls and her having the patience to let him work her, only taking charge when it was time to cum. When her limit was reached, she usually shoved his face onto her dick and held him there to pump her load directly into his mouth and stomach, but a few times he’d gotten his face coated in her cum, leaving him even more disheveled than his running makeup already made him look._

_Once he’d gotten used to her, though, she’d occasionally step things up, grabbing his hair and getting rougher, fucking his face in long, brutal thrusts that left him gagging and choking while she assured him that, no, he would not get a reprieve, and she expected him to enjoy this, even as her balls smacked his chin until she rammed her cum down his throat or spewed it all over his face. She seemed to delight in ruining the makeup that he had so meticulously applied, smearing his lipstick across her dick to mark how deep he’d taken her, leaving kiss marks on her balls, and scoring his face with running eyeliner and mascara._

_Sometimes she simply sat in her chair and lay back while he suckled her balls and worshiped her. She seemed to love the power she had over him, and though she wasn’t harsher on him then, the tenderness with which she treated him during those lazier moments seemed just as addictingly degrading._

_She blew her load fantastically every time, and always left him nursing a painful erection after giving her her oral pleasure. But he didn’t get the chance to jerk off until after she had left her cabin, thinking about her perfect, girthy dick and the nuts that gave her what she needed to cream his throat every time._

* * *

_She’d caught him, once, and had used her exaggerated disappointment to usher in the next stage in all this. When she’d begun requesting that he don clothes more fitting for his role._

_“Come on, dear,” she said, running her hands over his naked body, coursing over his smooth, supple skin. “Don’t you think that you deserve to look pretty? Besides, your captain wants you to be beautiful for her.”_

_He’d fidgeted and mumbled opposition, but quickly crumbled. She had a hold over him that he adored almost as much as he squirmed to escape it._

_Just bits and pieces, to begin. First, she’d asked him to start wearing panties underneath his trousers, something the rest of the crew couldn’t see even as his cock bulged within the tight confines of women’s underwear. Then, a bra beneath his shirt, similarly hidden, the fabric rubbing his nipples tightly, but not painfully._

_The crew probably already knew what was going on, given how much time he spent in her private quarters and how little work he did around the ship, but he tried to maintain the illusion of privacy and succeeded until she asked him to wear more openly feminine clothing._

_He’d refused, flatly. He wasn't ready, and she’d conceded and allowed him to advance to the less drastic change of high-heeled shoes. But he was starting to yearn for that full transition, to see what it would be like to become what she needed and wanted him to be._

_She promised him a reward the day he took the full plunge, even as she kept making use of his mouth while he dressed like a woman, and when his resistance to fully crossdressing finally broke, she was exuberant._

* * *

_“I’m so happy you finally accepted who you were meant to be.” She held him close, arms wrapped around him, heedless of how his face was pressing into her covered chest and her dick was rubbing against his thigh. “And now, you’ve earned your prize.”_

_After he sucked her off—but not enough to get her to cum, in spite of his desire to watch her face while she sighed or cackled and blew her load—she dressed him in clothes that were both similar and different to what she wore. The same corset and trousers, but so much skimpier than her captain's attire. Still, he did not feel shame. Only pride at how much fascination his effeminacy aroused in his Mistress. And she_ was _his mistress now: he had no illusions about that._

_It wasn’t long before she bent him over the bed, his skintight pantaloons pulled down to his knees, his panties pulled to the side, and his corset firmly fastened around his chest. Her spitshined dick nudged at his asshole while she positioned herself behind him, one hand on her cock to line it up with his tight, puckered rear, the other sinking into the soft skin of his butt._

_“That’s it, relax...you’re so, so gorgeous, my sweet…” Miss Fortune whispered as the head of her shaft prodded insistently on that unyielding entrance. He tried to relax, gripping the sheets and biting his lip, the smaller captain’s hat on his head shuddering atop his frizzy red hair._

_Miss Fortune probably could have used lube, but it was so much more_ fun _to make her dear take it with only his own spit to ease it along. He whimpered and felt his back arch, and then she was entering him._

_“There, that’s not so bad, is it? Just a little push, and…”_

_The tip of her dick slipped into his rear, and he let out a high little whine at the intrusion._

_“Shh, sweetie...be a good girl and open up your ass more for me, okay?” Fortune said, her fingers digging softly into his ripe, round asscheeks as she went. “I know you want it as bad as I do~.”_

_He let out a breath and hissed, and his rear widened for her cock. She slid forward, her dick plugging his butt with an almost elegant smoothness, and then she was finally halfway in._

_“Oooh~!” She crooned, leaning forward to drape herself across his back, her tits squishing up against the bottom of his shoulders while her nipples dug into the fabric of his corset. “A perfect fit. You’re a treasure."_

_As she sank deeper, her breasts dragged upwards, prodding the bare skin of his upper shoulders when she was most of the way in. He was hyperventilating, trying to maintain his focus even as she introduced him to his first chapter in anal intercourse._

_“Almost...just a bit more, darling.” Miss...no,_ Mistress _Fortune said, an edge to her voice that told him that she was closer perhaps to cumming than to bottoming out in him. He wasn’t sure what he wanted first: her climax, or the satisfaction of taking her all the way._

_“Annnnd...all the way in~.” She cooed in a singsong voice, her lips near his ear, licking and nibbling at the lobe while the captain’s hat slid off his head. “You’re such a good girl. Get ready for the rest of your reward!”_

_She slipped her cock in and out, never withdrawing more than half of her fat, lengthy dick before sliding back forward. Mercifully, she didn’t ream him out, or pound him roughly, or rearrange his guts too forcefully, but even at her subdued, self-controlled pace he still found himself straining to take it all._

_All the pressure, all the heat, all the tension...to say nothing of the effect of her tits on his back sliding with her movements; or the light tapping of her bigger balls against his when she speared him fully; or her mouth by his head, encouraging him all the while. The head of her cock kept nudging a tiny, hard bud inside of him that left his knees trembling from the sensitivity._

_“So tight...and so warm...oh, you have_ no _idea how long I’ve wanted something like this. How long I’ve needed someone like you. But you can feel it, can’t you? You can feel how much I’ve been looking forward to this...and how much more there’ll be, dear.”_

_She spoke softly, but posessively, and yet he felt no fear. No regret. Nothing could have exceeded the joy of this moment, of Mistress Fortune fucking him right up the ass while he begged for it and lay in wait for the inevitable, wonderful end result._

_“I’m...oh, I can’t hold it in any longer, my good girl. Here it comes. There’s going to be so, so many more where this came from, honey~!”_

_Sarah Fortune bottomed out in his butt, her languid pace enough to let her reach her peak, and her balls pulsed and throbbed while she emptied them into his rear. He mewled and squirmed while her load and the head of her cock brushed against his prostate, her whole body atop him and controlling him with her weight._

_The heft of her tits against his back...the cream filling his rear...the slutty clothes that were moved out of the way for his effeminate form to be put even more on display for her...the energy and passion of Sarah Fortune...it was all too much for him to handle. He came, smaller dick twitching and firing his own prodigious cream deep into the covers of her bed while it ground against the fabric and Sarah moved with him, still hard and still blasting spunk up his ass, so much that he wondered if it would overflow from around where her dick was stuffed into his rear._

_“That’s it, let it all out...it feels so good to cum the way you’re meant to, doesn’t it?” She kissed the back of his neck and he felt her smile against his skin. “I’m so proud of you.”_

_In his own chest, the same warmth swelled within him. He was happy._

* * *

_That had been quite some time ago._

_Since then, he had done a lot more with her. Whether it was his mouth, his ass, or some combination of the two or even the rest of his body, he satisfied her however she needed him to, and he enjoyed every bit of it._

_She’d spared him that first day, and they’d since had plenty of sweet, adoring rounds of lovemaking, with her reaching around for his dick while spooning and fucking him from behind as they kissed, or gently slipping it to him face-to-face so they could moan into each other’s mouths as her tits pushed against his chest, to name but a few, firing her cum in his rear or on his skin as she liked._

_She’d also taken the liberty of getting rougher once he’d been broken in. He’d ridden her on her bed while his cock swiveled and scattered his cum; he’d been fucked with her holding him upright against the wall of her cabin; he’d been pressed into the floor while she hoisted his legs up and bent them so his knees touched the ground near his head and her breasts swung forward and back with her pounding. Every time, she either flooded his butt with her warm cream or scattered it across the outside of his body, depositing copious loads however she pleased. To say nothing of his continued oral tributes, or the times when she got creative with his hands or the rest of him…_

_But she still found time to take it slow, to treat him like the precious person he knew he was._

_He had fully grown into the role his captain and Mistress demanded him. He was a valued part of her crew, and her dearest companion in more ways than one. For all intents and purposes, he looked like another Miss Fortune but even more feminine. Having sex with her felt like gazing into a mirror...if the reflection he saw was taller, stronger, more muscular, more freckled, wider-hipped and sporting deliciously massive tits, and wielding a cock and a pair of balls of far mightier size._

_So, a pretty close match._

* * *

All these memories came back to him now, as Captain Sarah Fortune stepped through the door of her cabin and locked the deadbolt. That wasn’t to keep him in, for he would never leave her if he could help it. It was to secure a bit of privacy from the prying eyes of her crew. A group of people that, quite obviously, already knew what was going on.

How would she have him today? There were so many options at their disposal, but watching her approach, her gaze adoring and her smile gentle, he couldn’t stop himself from trembling, overcome with joy.

He was the most beautiful woman that Sarah Fortune had ever seen, and she would never make him feel anything but treasured.

**Author's Note:**

> I'm also on [twitter](https://twitter.com/Lewdsmoke) and [ Hentai Foundry](http://www.hentai-foundry.com/user/Lewdsmokesoldier/profile).


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